Abstract
Abstract The Claisen rearrangement of allyl o- or p-hydroxyphenyl ether is catalyzed by alkali metal salts. The mechanism of the catalytic effect is different from that by Lewis acids such as zinc chloride. It is considered that the hydroxyl group is dissociated into phenoxide ion –O− with loss of its proton through attack by the anion residue of an alkali metal salt. Thus, the catalytic effect is attributable to a strong electron-releasing effect of phenoxide ion –O−. Furthermore, for the o-isomer, an intramolecular repulsion between the phenoxide ion –O− and the ethereal oxygen operates.
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